Complexes of fluconazole with sodium p-sulfonatocalix[n]arenes: characterization, solubility and antifungal activity

被引：29

作者：

Abranches, P. A. S. ^{[1
]}

Varejao, E. V. V. ^{[1
]}

da Silva, C. M. ^{[2
]}

de Fatima, A. ^{[2
]}

Magalhaes, T. F. F. ^{[3
]}

da Silva, D. L. ^{[3
]}

de Resende-Stoianoff, M. A. ^{[3
]}

Reis, S. ^{[4
]}

Nascimento, C. S., Jr. ^{[4
]}

de Almeida, W. B. ^{[5
]}

Figueiredo, I. M. ^{[6
]}

Fernandes, S. A. ^{[1
]}

机构：

[1] Univ Fed Vicosa, CCE, Dept Quim, BR-36570900 Vicosa, MG, Brazil

[2] Univ Fed Minas Gerais, ICEx, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil

[3] Univ Fed Minas Gerais, ICB, Dept Microbiol, BR-31270901 Belo Horizonte, MG, Brazil

[4] Univ Fed Sao Joao Del Rei, Dept Ciencias Nat DCNAT, BR-36301160 Sao Joao Del Rei, MG, Brazil

[5] Univ Fed Fluminense, Inst Quim, Dept Quim Inorgan, LQC, BR-24020141 Niteroi, RJ, Brazil

[6] Univ Fed Alagoas, Inst Quim & Biotecnol, BR-57072900 Maceio, AL, Brazil

来源：

RSC ADVANCES | 2015年 / 5卷 / 55期

关键词：

NUCLEAR-MAGNETIC-RESONANCE; P-SULFONIC ACID; STUDYING TRANSLATIONAL DIFFUSION; BETA-CYCLODEXTRINS; NMR; GUEST; ASPERGILLOSIS; EXCHANGE; ARENES; TOOL;

D O I：

10.1039/c5ra05423k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aiming at providing new formulations capable of improving the biopharmaceutical properties of fluconazole, we studied the formation of host-guest complexes of this antifungal agent with water-soluble sodium p-sulfonatocalix[4]arene and sodium p-sulfonatocalix[6]arene. The formation of inclusion complexes was first investigated using H-1 NMR spectroscopy and TGA experiments. The complexes' stoichiometry, apparent binding constants (K-a) and the complexed populations (%p(bound)), were determined, using H-1 NMR data. The topology of the complexes were assessed by 1D ROESY experiments, and the data were corroborated by semi-empirical and DFT calculations. The activity of the fluconazole-calix[n]arene complexes against clinically relevant fungal species was investigated. Finally, the effect of complexation on the solubility of fluconazole was investigated using the phase-solubility method of Higuchi and Connors.

引用

页码：44317 / 44325

页数：9

共 63 条

[1] Current status of antifungal resistance and its impact on clinical practice [J].

Alcazar-Fuoli, Laura ;

Mellado, Emilia .

BRITISH JOURNAL OF HAEMATOLOGY, 2014, 166 (04) :471-484

[2]

[Anonymous], PULM PHARM THER

[3]

[Anonymous], 2009, INT J CHEM TECH RES

[4]

[Anonymous], SPECTROSCOPY

[5]

[Anonymous], SPANISH J CHEMOTHERA

[6] Benzocaine Complexation with p-Sulfonic Acid Calix[ n] arene: Experimental ( 1 H-NMR) and Theoretical Approaches [J].

Arantes, Lucas M. ;

Varejao, Eduardo V. V. ;

Pelizzaro-Rocha, Karin J. ;

Cereda, Cintia M. S. ;

de Paula, Eneida ;

Lourenco, Maicon P. ;

Duarte, Helio A. ;

Fernandes, Sergio A. .

CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 83 (05) :550-559

[7] Proparacaine complexation with β-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied 1H-NMR approaches [J].

Arantes, Lucas Micqueias ;

Scarelli, Camilla ;

Marsaioli, Anita Jocelyne ;

de Paula, Eneida ;

Fernandes, Sergio Antonio .

MAGNETIC RESONANCE IN CHEMISTRY, 2009, 47 (09) :757-763

[8] A new definition of cavities for the computation of solvation free energies by the polarizable continuum model [J].

Barone, V ;

Cossi, M ;

Tomasi, J .

JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) :3210-3221

[9] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[10] Structural analysis of cyclodextrins: A comparative study of classical and quantummechanical methods [J].

Britto, MAFO ;

Nascimento, CS ;

dos Santos, HF .

QUIMICA NOVA, 2004, 27 (06) :882-888

← 1 2 3 4 5 6 7 →